Hydrochloric Acid → HCID 10845683, compound

HRID 2210435Notes

Reaction equation

HRID 2210435 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].C=O.[C:15](OCC)(=O)C.Cl>C(O)(C)C>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[S:9](=[O:11])(=[O:10])[NH:12][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 15365170HCID 15365170, compound

Product 1

HCID 10845683HCID 10845683, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1 g of 4-methylaminopyridine-3- sulfonamide (Preparation 6) and 1 g of paraformaldehyde (excess) in 10 cm3 of isopropanol to which 4 cm3 of ethyl acetate saturated with gaseous HCl have been added is brought to reflux for 10 hours. After this lapse of time, the solvent is removed under partial vacuum (rotary evaporator) and the residue is redissolved in methanol. A possible insoluble material is filtered and the filtrate, to which 2 volumes of diethyl ether have been added, is left to precipitate the title compound in the form of crystals. The crystals are collected on a filter, washed with diethyl ether and dried. Yd. : 60-65% M.p. (hydrochloride): 291-294° C.

Workup

  1. additionhave been added
  2. temperatureto reflux for 10 hours
  3. customAfter this lapse of time, the solvent is removed under partial vacuum (rotary evaporator)
  4. dissolutionthe residue is redissolved in methanol
  5. filtrationA possible insoluble material is filtered
  6. additionthe filtrate, to which 2 volumes of diethyl ether have been added
  7. waitis left
  8. customto precipitate the title compound in the form of crystals
  9. customThe crystals are collected on a filter
  10. washwashed with diethyl ether
  11. customdried
  12. custom291-294° C.

Sources & evidence

ORD record
ord-4f7883003dc245ceba721f8526cb316e
Source dataset
uspto-grants-1995_10
Patent number
US05459138

Reaction notes

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